L-Serine → 2-Methyl Oleoyl-L-Serine

HRID 218122

반응식

HRID 218122 반응식
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+].[CH3:19][CH:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:21](O)=[O:22]>O1CCCC1>[CH3:19][CH:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[C:21]([NH:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4])=[O:22]

참가 물질

6

반응물 4

HCID 5951L-SerineHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 99222352-Methyl oleic acid

생성물 1

HCID 469122122-Methyl Oleoyl-L-Serine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
35 °C

실험 절차

A solution of L-serine (190 mg, 1.8 mmol) in 20 ml. of 0.1 N sodium carbonate and 0.1 N sodium bicarbonate was added to a solution of N-hydroxysuccinimide ester of 2-methyl oleic acid (204.5 mg, 0.5 mmole) in 20 ml tetrahydrofuran. The reaction mixture was stirred overnight at 35° C., evaporated down to 20 ml, and acidified to pH 1 with 1 N HCl. The product was extracted with methylene chloride (2×20 mL), dried (MgSO4), and the solvent evaporated under reduced pressure. The crude material was chromatographed on silica gel (eluting with chloroform:methanol) to give 86 mg (45%) as a yellowish oil 1H NMR (CDCl3) δ 0.912 (t, 3H), 1.129 (d, 3H), 1.288 (s, 20H), 1.611 (m, 2H), 2.018 (m, 4H), 2.323 (m. 1H), 3.787 (dd, 1H), 3.980 (dd, 1H), 4.503 (t, 1H), 5.353 (m, 2H).

후처리

  1. customevaporated down to 20 ml
  2. extractionThe product was extracted with methylene chloride (2×20 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated under reduced pressure
  5. customThe crude material was chromatographed on silica gel (eluting with chloroform:methanol)

출처 및 근거

ORD 기록
ord-53031352c4a047ffac300995c5a3175e
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198327B2

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